


Pretty Boy Dean

by fuckingtyler



Category: Supernatural
Genre: Hunters & Hunting, M/M, Other Additional Tags to Be Added, Stripper Dean Winchester
Language: English
Status: Completed
Published: 2019-01-28
Updated: 2019-01-28
Packaged: 2019-10-18 16:28:06
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 1,465
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17584343
Author URL: https://archiveofourown.org/users/fuckingtyler/pseuds/fuckingtyler
Summary: Dean was just trying to make some extra money while John was out on a trip longer than expected. It was just supposed to be something he did once and forgot about the second they were out of the state.





	Pretty Boy Dean

Dean sighed as he made his way into the dark motel room quietly. It was almost four am and Sam was probably sleeping so he had to be quiet. He closed the door behind him gently, setting his bag down on the empty bed. He grabbed a pair of boxers and a shirt from the bag and made his way to the bathroom. He turned on the light and shut the door behind him. His entire body was sore and all he wanted to do was lay down. John was on a hunt and had been for about two weeks now. The money they were left with was almost gone because John only expected to be gone for no more than a week. John had called and said it was a lot worse than he had thought and he’d been gone for probably a month or so. Dean couldn’t find a decent job for the life of him. So, with the fake ID’s John made him, he started working at a strip club. He was only a few months away from eighteen anyways. He just told Sam he was bar tending since that would make the late nights not so suspicious. Dean had no idea what he was doing when he got into it but he learned fairly quickly. It was easy for him to put on a flirty front, but it was difficult to do it with men. It definitely took Dean some getting used to since had little to no experience with men, but there were no male strip clubs in the area that weren’t just for men. He had been working for the past week straight to get used to everything and he was regretting it majorly. 

Dean groaned and whined as he got undressed because of how stiff and sore he was. He tossed his clothes aside and pulled on a clean pair of boxers and a plain t shirt. He opened the bathroom door and turned off the light before he grabbed the bad on his bed and shoved it underneath the bed. He then crashed down onto the empty bed. He made noises of discomfort as he climbed under the covers and finally laid his head down on the pillow with a sigh of relief. He had the next couple of days off but Sam was going to be in school anyways. He thought about just going to work tomorrow to have something to do and they needed the money anyways. Apparently Monday’s were always busy and full of business men who’s Monday’s were rough and needed to relax and complain to a bunch of strippers. Dean knew he’d make good money but he was so sore. He’d think about it in the morning. He closed his eyes and finally started to fall asleep, completely relaxing into his bed. 

Dean woke up in the morning to Sam shaking him awake. His eyes fluttered open slowly as he looked up at Sam. He groaned quietly as he slowly sat up. He knew he had to drop off Sam at school but he really did not have the energy at all. He was even more sore now after sleeping. Dean sighed and rubbed his eyes tiredly. 

“Mornin’, Sammy. Are we leaving?” He asked tiredly. He watched as Sam sat down on the edge of the bed next to Dean, shaking his head. 

“No, I know you were working really late so I asked a friend if they could pick me up. They’re here right now.” Sam said with a smile. Dean smiled back tiredly. 

“Ah, Sammy, you’re the best... you got everything you need? Your knife? Salt? Holy water?” He asked, already knowing the answer was yes, but he always wanted to make sure. Sam nodded, rolling his eyes dramatically. 

“Yes, Dean, you ask me this everyday.” His brother said as he stood up. “I’ll see you after school. Bye!” He watched as Sam waved before going outside. He heard a car door open and shut before he heard it drive away. Dean sighed as he laid back down and within minutes he was passed out again. He was sleeping good until he was woken up by his phone ringing. He groaned loudly, almost not wanting to pick it up, but he knew he had to. While his eyes were still closed, Dean reached over and grabbed his phone from the nightstand. It was just the manager from the club, asking if he wanted to work today. After a moment of hesitation he said yes. Then the manager proceeded to tell him about a man who came in and asked for Dean specifically. Dean frowned at that, there’s no way that was a good thing. Apparently someone came in a couple days ago and saw Dean but was “too afraid” to talk to him. Once his boss hung up, he looked at the time and saw that he had a couple hours until he had to go into work. He knew if he went back to sleep he wouldn’t want to get up so he sat up, rubbing his eyes as he sighed. 

Dean stood up, groaning softly in discomfort. He stretched a bit, putting his arms behind his back and pushing them out as he turned his back to pop it. He sighed as he walked over to his bags and found something to wear. He pulled on a pair of jeans and put a flannel on over his shirt. He grabbed his keys and jacket before he made his way out to the car. Dean got in and after he turned on the car, he made his way out of the motel parking lot. He found the closest restaurant and pulled into it, getting out of the car before he went inside. He sat himself down in a booth and a waitress gave him a menu and filled an empty cup with ice water, setting it down in front of Dean. She gave him a sweet smile before she walked away. Before he picked up his menu, he glanced up, making eye contact with a man. He frowned slightly. A dark haired man in a suit was staring at him, quite intensely too. The mans tie was messy along with his hair and the white button up shirt he wore was wrinkled. His suit jacket had a tear in it by the shoulder, seemingly from a knife. Dean clenched his jaw a bit. It looked the man had just gotten into a fight. The next thing he knew the older man was getting up and grabbing his coat before making his way out of the restaurant. Dean watched him go with a confused look on his face. The guy looked at Dean like he knew him almost or, at least, knew of him. Dean sighed, shaking his head a bit. He’s sure it was nothing. He ordered a burger and soda when the waitress came back, handing her his menu before she walked away. 

When Dean got his food, he ate it slowly, trying to waste some time. By the time he was done, he had wasted an hour or so. He made his way back to the motel, parking the car when he got there and he made his way inside. He grabbed his bag from under his bed and opened it with a sigh. It was full of different kinds of lingerie that he wore at the club, along with a gun and his flask of some salted holy water. Everything in it, lingerie wise, was picked out by a guy from work. Alfie had been working there for a lot longer than Dean and knew what the guys like to see. Also, according to him, he knew what Dean would look good in. Dean still didn’t know how to feel about all of this, but he didn’t exactly hate it. He knew he was good looking, he had been sweet talking girls since kindergarten and he was always good at it. He knew what girls liked to hear, he thought it’d be different with men, and it was, but it came to him just as naturally. He just had to play weak and dumb, he acted like he was just a pretty face and it worked. Hell, the first night he was at the club he made almost a grand. Besides, he had the attributes of any good stripper. High school dropout with daddy issues all wrapped up in a pretty package topped with freckles and a sinful mouth. 

Dean zipped up his bag, slinging it over his shoulder before he made his way outside. He locked the motel door and got in his car, tossing his bag into the passengers seat as he drove off.


End file.
